Tetrabutylammonium Fluoride → tert-Butyl 4-((6-(hydroxymethyl)pyridin-2-yl)oxy)piperidine-1-carboxylate

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Reaction Steps

To a solution of tert-butyl 4-{[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-yl]oxy}piperidine-1-carboxylate (0.50 g, 1.18 mmol) in THF (8 mL) was added tetrabutylammonium fluoride (1.78 mL, 1.0 M in THF, 1.78 mmol). The resulting mixture was stirred at room temperature for 1 hour, concentrated and purified by flash chromatography using a gradient run from 5-100% EtOAc in toluene. The selected fractions were concentrated in vacuo to give the product as a clear oil. Yield: 0.34 g (93%). 1H NMR (400 MHz, CDCl3) δ 7.54 (t, 1H, J=7.66 Hz), 6.78 (d, 1H, J=7.26 Hz), 6.59 (d, 1H, J=8.16 Hz), 5.15-5.26 (m, 1H), 4.62 (s, 2H), 3.66-3.77 (m, 2H), 3.25-3.37 (m, 3H), 1.89-1.99 (m, 2H), 1.59-1.82 (m, 2H), 1.45 (s, 9H).

Provenance & Evidence